Various phenylcarbamoylbenzimidates were prepared in conjunction with a study on the structure of carbamoylamidoximes by R. Boyle, et al., Helv. Chim. Acta., 46, 1073 (1963).
Various substituted phenylcarbamoylbenzimidates and their use as insecticides and insect growth regulators are disclosed in my copending application Ser. No. 223,009, filed Feb. 9, 1981 and a continuation-in-part thereof, filed concurrent herewith.
Various 2,6-difluoro-benzoylimidates, including ethyl 2,6-difluoro-N-[[[4-(2-chloro-4-trifluoromethylphenoxy)phenyl]amino]carbon yl]benzenecarboximidate, are described as insecticides especially effective against lepidopterous and coleopterous insects in European Patent application Number 79300868.1 filed 18/5/79 and published 12/12/79 with a Publication Number: 0 005 944. See also U.S. Pat. No. 4,200,653.
Various benzoylureas have been described in the literature and patents as insecticides including those described in U.S. Pat. Nos. 3,748,356, 4,103,022, 4,160,834, 4,170,657 and others. See also German Offenlegungsschrift No. 2,801,316.
U.S. Pat. No. 4,170,657 describes various substitueted (((phenyl)amino)carbonyl)benzamides as insecticides including:
2-chloro-N-(((4-trifluoromethoxy)phenyl)amino)carbonyl)benzamide, PA0 2-trifluoromethyl-N-(((4-trifluoromethoxy)phenyl)amino)carbonyl)benzamide, PA0 2,6-difluoro-N-(((4-(1,1,2,2-tetrafluoroethoxy)phenyl)amino)carbonyl)benzam ide, PA0 2,6-difluoro-N-(((4-(2,2-dichooro-1,1-difluoroethoxy)phenyl)amino)carbonyl) benzamide, PA0 2,6-difluoro-N-(((4-(trifluoromethoxy)-phenyl)amino)carbonyl)benzamide, PA0 2,6-dichloro-N-(((4-(trifluoromethoxy)phenyl)amino)carbonyl)benzamide, PA0 2,6-dimethoxy-N-(((4-(1,1,2,2-tetrafluoroethoxy)phenyl)amino)carbonyl)benza mide, PA0 2,6-dichloro-N-(((2-(2,2-dichloro-1,1-difluoroethoxy)phenyl)amino)carbonyl) benzamide, PA0 2,6-dichloro-N-(((4-(2,2-dichloro-1,1-difluoroethoxy)phenyl)amino)carbonyl) -N-methylbenzamide, PA0 2-chloro-N-(4-(((2,2-dichloro-1,1-difluoroethylthio)phenyl)amino)carbonyl)b enzamide, PA0 2,6-dichloro-N-(((4-((2,2-dichloro-1,1-difluoroethyl)thio)phenyl)amino)carb onyl)benzamide, PA0 2-chloro-N-(((2-(2,2-dichloro-1,1-difluoroethoxy)phenyl)amino)carbonyl)benz amide, PA0 2-chloro-N-(((4-(1,1,2,2-tetrafluoroethoxy)phenyl)amino)carbonyl)benzamide, PA0 2,6-dibromo-N-(((4-(1,1,2,2-tetrafluoroethoxy)phenyl)amino)carbonyl)benzami de, PA0 2,6-dichloro-N-(((4-(2,2-dichloro-1,1-difluoroethoxy)phenyl)methylamino)car bonyl)benzamide, PA0 2,6-difluoro-N-(((4-(2,2-dichloro-1,1-difluoroethoxy)phenyl)methylamino)car bonyl)benzamide, PA0 2-bromo-N-(((4-(1,1,2,2-tetrafluoroethoxy)phenyl)amino)carbonyl)benzamide, PA0 2,6-dichloro-N-(((3-(2,2-dichloro-1,1-difluoroethoxy)phenyl)amino)carbonyl) benzamide, PA0 2-chloro-N-(((4-(2,2-dichloro-1,1-difluoroethoxy)phenyl)methylamino)carbony l)benzamide, PA0 2,6-difluoro-N-(((3-(2,2-dichloro-1,1-difluoroethoxy)phenyl)amino)carbonyl) benzamide, PA0 2,6-difluoro-N-(((2-(2,2-dichloro-1,1-difluoroethoxy)phenyl)amino)carbonyl) benzamide, PA0 2-trifluoromethyl-N-(((4-(2,2-dichloro-1,1-difluoroethoxy)phenyl)methylamin o)carbonyl)benzamide, PA0 2-fluoro-N-(((4-(1,1,2,2-tetrafluoroethoxy)phenyl)amino)carbonyl)benzamide, PA0 2,6-difluoro-N-(((4-((2,2-dichloro-1,1-difluoroethyl)thio)phenyl)amino)carb onyl)benzamide, PA0 2,6-difluoro-N-(((4-((1,1,2,2-tetrafluoroethyl)thio)phenyl)amino)carbonyl)b enzamide, PA0 2,6-dichloro-N-(((4-((1,1,2,2-tetrafluoroethyl)thio)phenyl)amino)carbonyl)b enzamide, PA0 2,6-dichloro-N-(((4-(2,2-dichloro-1,1-difluoroethoxy)phenyl)amino)carbonyl) benzamide, PA0 2,6-dichloro-N-(((4-(1,1,2,2-tetrafluoroethoxy)phenyl)amino)carbonyl)benzam ide, and PA0 2-chloro-N-(((4-(2,2-dichloro-1,1-difluoroethoxy)phenyl)amino)carbonyl)benz amide PA0 Methyl 2-chloro-N-[[[4-(trifluoromethoxy)phenyl]amino]carbonyl]benzenecarboximida te, PA0 Ethyl 2-chloro-N-[[[4-(trifluoromethoxy)phenyl]amino]carbonyl]benzenecarboximida te, PA0 Ethyl 2,6-difluoro-N-[[[4-(trifluoromethoxy)phenyl]amino]carbonyl]benzenecarboxi midate, PA0 Ethyl 2-fluoro-N-[[[4-(trifluoromethoxy)phenyl]amino]carbonyl]benzenecarboximida te, PA0 Methyl 2,6-dichloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate, PA0 Methyl 2-trifluoromethyl-N-[[[4-(trifluoromethoxy)phenyl]amino]carbonyl]benzeneca rboximidate, PA0 Methyl 2,6-dichloro-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benze necarboximidate, PA0 Methyl 2,6-dichloro-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benze necarboximidate, PA0 Methyl 2,6-difluoro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate, PA0 Methyl 2,6-difluoro-N-[[[4-(trifluoromethoxy)phenyl]amino]carbonyl]benzenecarboxi midate, PA0 Methyl 2,6-difluoro-N-[[[2-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate, PA0 Methyl 2,6-difluoro-N-[[[4-((2,2-dichloro-1,1-difluoroethyl)thio)phenyl]amino]car bonyl]benzenecarboximidate, PA0 Methyl 2,6-dimethoxy-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benz enecarboximidate, PA0 Methyl 2,6-dichloro-N-[[[2-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate, PA0 Methyl 2,6-dichloro-N-[[[4-((2,2-dichloro-1,1-difluoroethyl)thio)phenyl]amino]car bonyl]benzenecarboximidate, PA0 Methyl 2-chloro-N-[[[2-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl]ben zenecarboximidate, PA0 Methyl 2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl]ben zenecarboximidate, PA0 Methyl 2-chloro-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benzeneca rboximidate, PA0 Methyl 2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethylthio)phenyl]amino]carbonyl] benzenecarboximidate, PA0 Methyl 2,6-dichloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]methylamino]ca rbonyl]benzenecarboximidate, PA0 Methyl 2,6-difluoro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]methylamino]ca rbonyl]benzenecarboximidate, PA0 Methyl 2,6-dibromo-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benzen ecarboximidate, PA0 Methyl 2-bromo-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benzenecar boximidate, PA0 Methyl 2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]methylamino]carbon yl]benzenecarboximidate, PA0 Methyl 2-fluoro-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benzeneca rboximidate, PA0 Methyl 2-trifluoromethyl-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]methyl]am ino]carbonyl]benzenecarboximidate, PA0 Methyl 2,6-difluoro-N-[[[3-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate, PA0 Methyl 2,6-dichloro-N-[[[3-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate, PA0 Methyl 2,6-difluoro-N-[[[4-((1,1,2,2-tetrafluoroethyl)thio)phenyl]amino]carbonyl] benzenecarboximidate, PA0 Methyl 2,6-dichloro-N-[[[4-((1,1,2,2-tetrafluoroethyl)thio)phenyl]amino]carbonyl] benzenecarboximidate, PA0 Ethyl 2,6-dichloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate, PA0 Ethyl 2-trifluoromethyl-N-[[[4-(trifluoromethoxy)phenyl]amino]carbonyl]benzeneca rboximidate, PA0 Ethyl 2,6-dichloro-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benze necarboximidate, PA0 Ethyl 2,6-dichloro-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benze necarboximidate, PA0 Ethyl 2,6-difluoro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate, PA0 Ethyl 2,6-difluoro-N-[[[4-(trifluoromethoxy)phenyl]amino]carbonyl]benzenecarboxi midate, PA0 Ethyl 2,6-difluoro-N-[[[2-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate, PA0 Ethyl 2,6-difluoro-N-[[[4-((2,2-dichloro-1,1-difluoroethyl)thio)phenyl]amino]car bonyl]benzenecarboximidate, PA0 Ethyl 2,6-dimethoxy-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benz enecarboximidate, PA0 Ethyl 2,6-dichloro-N-[[[2-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate, PA0 Ethyl 2,6-dichloro-N-[[[4-((2,2-dichloro-1,1-difluoroethyl)thio)phenyl]amino]car bonyl]benzenecarboximidate, PA0 Ethyl 2-chloro-N-[[[2-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl]ben zenecarboximidate, PA0 Ethyl 2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl]ben zenecarboximidate, PA0 Ethyl 2-chloro-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benzeneca rboximidate, PA0 Ethyl 2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethylthio)phenyl]amino]carbonyl] benzenecarboximidate, PA0 Ethyl 2,6-dichloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]methylamino]ca rbonyl]benzenecarboximidate, PA0 Ethyl 2,6-difluoro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]methylamino]ca rbonyl]benzenecarboximidate, PA0 Ethyl 2,6-dibromo-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benzen ecarboximidate, PA0 Ethyl 2-bromo-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benzenecar boximidate, PA0 Ethyl 2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]methylamino]carbon yl]benzenecarboximidate, PA0 Ethyl 2-fluoro-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benzeneca rboximidate, PA0 Ethyl 2-trifluoromethyl-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]methylami no]carbonyl]benzenecarboximidate, PA0 Ethyl 2,6-difluoro-N-[[[B 3-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl]benzenecarboximid ate, PA0 Ethyl 2,6-dichloro-N-[[[3-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate, PA0 Ethyl 2,6-difluoro-N-[[[4-((1,1,2,2-tetrafluoroethyl)thio)phenyl]amino]carbonyl] benzenecarboximidate, PA0 Ethyl 2,6-dichloro-N-[[[4-((1,1,2,2-tetrafluoroethyl)thio)phenyl]amino]carbonyl] benzenecarboximidate, PA0 1-Methylethyl 2,6-dichloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate, PA0 1-Methylethyl 2-trifluoromethyl-N-[[[4-(trifluoromethoxy)phenyl]amino]carbonyl]benzeneca rboximidate, PA0 1-Methylethyl 2,6-dichloro-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benze necarboximidate, PA0 1-Methylethyl 2,6-dichloro-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benze necarboximidate, PA0 1-Methylethyl 2,6-difluoro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate, PA0 1-Methylethyl 2,6-difluoro-N-[[[4-(trifluoromethoxy)phenyl]amino]carbonyl]benzenecarboxi midate, PA0 1-Methylethyl 2,6-difluoro-N-[[[2-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate, PA0 1-Methylethyl 2,6-difluoro-N-[[[4-((2,2-dichloro-1,1-difluoroethyl)thio)phenyl]amino]car bonyl]benzenecarboximidate, PA0 1-Methylethyl 2,6-dimethoxy-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benz enecarboximidate, PA0 1-Methylethyl 2,6-dichloro-N-[[[2-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate, PA0 1-Methylethyl 2,6-dichloro-N-[[[4-((2,2-dichloro-1,1-difluoroethyl)thio)phenyl]amino]car bonyl]benzenecarboximidate, PA0 1-Methylethyl 2-chloro-N-[[[2-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl]ben zenecarboximidate, PA0 1-Methylethyl 2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl]ben zenecarboximidate, PA0 1-Methylethyl 2-chloro-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benzeneca rboximidate, PA0 1-Methylethyl 2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethylthio)phenyl]amino]carbonyl] benzenecarboximidate, PA0 1-Methylethyl 2,6-dichloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]methylamino]ca rbonyl]benzenecarboximidate, PA0 1-Methylethyl 2,6-difluoro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]methylamino]ca rbonyl]benzenecarboximidate, PA0 1-Methylethyl 2,6-dibromo-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benzen ecarboximidate, PA0 1-Methylethyl 2-bromo-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benzenecar boximidate, PA0 1-Methylethyl 2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]methylamino]carbon yl]benzenecarboximidate, PA0 1-Methylethyl 2-fluoro-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benzeneca rboximidate, PA0 1-Methylethyl 2-trifluoromethyl-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]methylami no]carbonyl]benzenecarboximidate, PA0 1-Methylethyl 2,6-difluoro-N-[[[3-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximdate, PA0 1-Methylethyl 2,6-dichloro-N-[[[3-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate, PA0 1-Methylethyl 2,6-difluoro-N-[[[4-((1,1,2,2-tetrafluoroethyl)thio)phenyl]amino]carbonyl] benzenecarboximidate, PA0 1-Methylethyl 2,6-dichloro-N-[[[4-((1,1,2,2-tetrafluoroethyl)thio)phenyl]amino]carbonyl] benzenecarboximidate.
German Offenlegungsschrift No. 2,801,316 describes varius N-phenyl-N'-(2-chloro-6-fluorobenzoyl)urea derivatives as effective against animal parasites and as effective against insects, spiders and nematodes.